Lithium borohydride → HCID 25029411, compound

HRID 1436402Notes

Reaction equation

HRID 1436402 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:13]3[C@H:17]([C:18](OC)=[O:19])[CH2:16][O:15][C:14]3=[O:22])[S:11][CH:12]=2)=[CH:4][CH:3]=1.[BH4-].[Li+]>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:13]3[C@H:17]([CH2:18][OH:19])[CH2:16][O:15][C:14]3=[O:22])[S:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 25029874HCID 25029874, compound

Product 1

HCID 25029411HCID 25029411, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl (4S)-3-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-2-oxo-1,3-oxazolidine-4-carboxylate (0.20 g, 0.52 mmol), prepared in step 2 of Example 70, was dissolved in 5 mL of tetrahydrofuran and cooled to 0° C. Lithium borohydride (2M solution in tetrahydrofuran, 0.57 mL, 1.14 mmol) was added and the mixture was stirred for 2 h. The mixture was allowed to warm to 25° C. and stirred for an additional 30 min, quenched with H2O and then 2 mL of 2N HCl was added. The mixture was diluted with 10 mL of water and poured into ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organics were combined and washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Flash chromatography (25% acetone/hexane) afforded the title compound (124 mg, 69%) as a white solid. mp 189-192° C. HRMS: calcd for C13H11BrN2O3S+H+, 354.97465; found (ESI, [M+H]+), 354.9742. Analytical HPLC: retention time 9.2 min, 210-370 nm the Xterra® RP18 column, 3.5μ, 150×4.6 mm 40° C. 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min, 1.2 mL/min 5 μL injection.

Workup

  1. temperatureto warm to 25° C.
  2. stirringstirred for an additional 30 min
  3. customquenched with H2O
  4. addition2 mL of 2N HCl was added
  5. additionThe mixture was diluted with 10 mL of water
  6. additionpoured into ethyl acetate
  7. customThe layers were separated
  8. extractionthe aqueous layer was extracted with ethyl acetate
  9. washwashed with water, brine
  10. dry with materialdried over anhydrous MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-632b9bebb50446f4b9abde01bea78e1b
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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